


Helping Hands

by ASchwartz33



Series: Wacky Adventures Aboard The Flying Thunder God [7]
Category: Naruto
Genre: Alternate Universe - Pirate, Anal Fingering, Anal Sex, Bottom Uchiha Itachi, Cousin Incest, Double Penetration, First Time, Gift Fic, Good Uchiha Obito, M/M, Pirates, Pirates with ninjutsu, Polyamorous pirate crew, Polyamory, Shameless Smut, Threesome - M/M/M, Top Uchiha Obito, Top Uchiha Shisui, Uchiha Obito-centric, Uchihacest
Language: English
Status: Completed
Published: 2020-07-08
Updated: 2020-07-08
Packaged: 2021-03-05 03:28:26
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 5,565
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25147726
Author URL: https://archiveofourown.org/users/ASchwartz33/pseuds/ASchwartz33
Summary: Written for @anannua for my 250 follower giveaway!Prompt request: Itachi/Shisui/Obito - smut. plot? what plot. Just a wild and rowdy night with straight up incestuous smutty sex.Part 7 of my ninja pirate au series!This takes place approx. 3 years BEFORE the main storyline.
Relationships: Hoshigaki Kisame/Uchiha Itachi, Uchiha Itachi/Uchiha Obito, Uchiha Itachi/Uchiha Shisui, Uchiha Obito/Uchiha Shisui
Series: Wacky Adventures Aboard The Flying Thunder God [7]
Series URL: https://archiveofourown.org/series/1732402
Comments: 9
Kudos: 88





	Helping Hands

**Author's Note:**

  * For [Anannua](https://archiveofourown.org/users/Anannua/gifts).



> Hey all! We're traveling back in time 3 years to witness the moment Itachi lost his virginity.  
> Ages in this fic:  
> Itachi -16  
> Shisui -17  
> Obito -21  
> Kisame -22

Obito strolled casually down the street. It wasn't everyday that they would dock in a village or port. It  _ also  _ wasn't everyday that  _ The Akatsuki  _ docked with them. It was a nice family reunion as Itachi and Shisui walked beside him. At 16, Itachi had barely been with the crew for 6 months, but Obito had felt a profound attachment towards his younger cousin. 

They had always known that Itachi would try to join up. As soon as they had found Shisui, the 14 year old had started telling tales of his adventures with his younger cousin. Honestly, now that he actually had gotten to  _ know  _ Itachi a bit, Obito was surprised he hadn't signed up at the same time as Shisui. 

Shisui had been sailing with them for 3 years now, and had proven himself an invaluable asset. He had brought with him answers of Obito's eyes and family, and the older pirate would always be grateful for that. 

It was a bit of a shock that Itachi had elected to wander with them instead of Kisame. The shark-man had grown an immediate attachment to the youngest Uchiha, and the two were hardly seen apart from each other. To be honest, Obito had hoped to drag Shisui into a room and have some good old fashioned fun.

"Shisui?" Itachi asked quietly, breaking the comfortable silence that had surrounded them. 

Obito looked past Shisui to see his younger cousin. Shisui was also watching him curiously. "Yeah?" 

"When did you lose your virginity?" Itachi asked, oblivious to the shocked faces on the older Uchihas. Obito couldn't comprehend how his  _ baby cousin  _ was asking such a thing. In reality, Itachi wasn't  _ that young _ . Obito himself had lost his at 17, and Shisui was only 15 when he lost his. Still, Itachi was different. He was far too  _ innocent  _ to be asking such things. He had such a young appearance, his looks bordering more on the feminine side.

"Uh… w-well…" Shisui stammered, looking just as confused as Obito. "I was 15." 

"Who was it?" Itachi asked, his face not showing any sign of being uncomfortable with the topic. 

Shisui was bright red, something that didn't happen all that often because Shisui was an absolute  _ pervert _ . Out of everyone on their crew, only  _ Kakashi  _ got more action than the teenager… and that was probably not always true. "Ah… well… I lost my virginity with  _ Kakashi _ ." Shisui finally managed to croak out. 

"Obito? How about you?" Itachi asked with a small smile, still oblivious to his flailing cousins. 

Obito froze. Perhaps this conversation was best had indoors instead of out in the street. Neither of his cousins fought him as he pulled them into the dark swirls of Kamui. His "mangekyou", as Shisui called it, had awakened nearly a year ago, when he was absolutely certain Kakashi had died. 

Thankfully, he had been wrong. The silver-haired pirate had held on long enough for Tenzo to save him, though the younger brunet had been an absolute  _ wreck  _ at the time. 

Now, his excessively useful jutsu set the three of them down in the room Obito had rented for the night. Shisui and Itachi were watching him expectantly, even though Shisui already knew Obito's answers. "I was 17, and I also lost mine to Kakashi."

Itachi nodded. "So Kakashi must have lost  _ his _ to you?" 

Obito laughed. "No way. Captain Minato beat me to it… if only by a few days." 

Thoughts of their awkward fumbling in the dark brought a smile to his face. Kakashi had been  _ so  _ happy to have a new way to express his feelings that he hadn't hesitated to share his findings with Obito. Even young  _ Tenzo  _ hadn't had to wait much longer after that to receive Kakashi's physical affections. 

"Ah. So Kakashi has had lots of partners?" Itachi inquired. 

It wasn't said as an insult. Obito knew this. Itachi didn't have a single  _ mean  _ bone in his body, and yet obito found himself nearly snarling at the sentence. Both cousins noticed, and Shisui's hands were on his shoulders in an instant. 

Shisui answered the question instead. "What you need to understand about Kakashi is that he is a very  _ physical  _ person. He doesn't like to express his feelings in words. He tends to show he cares through sex and physical affection, and there is nothing wrong with that." 

"Ah, I see. That is why he went with Gai tonight?" Itachi continued his line of questioning. 

"Yes." Obito replied with an exasperated sigh. He had a feeling that Itachi was hung up on the topic of virginity due to his very obvious attraction for Kisame, though he wasn't entirely sure why he was asking  _ them  _ about it. "Why? Have you lost your virginity, Itachi?" 

Itachi huffed, showing some rare annoyance.  _ "No.  _ That is the problem. Kisame refuses to be my first." 

"Why?" Shisui asked incredulously. 

Itachi sighed, sitting down on the edge of the bed. "I'm not entirely sure. He had a bad experience. He says he is too…  _ large  _ to be someone's first." 

Obito shared a glance with Shisui. Neither of them had ever been with the water-style user from their sister ship. The guy didn't exactly  _ respond _ to flirting and innuendos. Perhaps  _ now  _ they knew why. 

"Oh." Obito replied quietly. Taking a seat next to Itachi while Shisui sat on the other side. "Did you… want advice?" 

"Or suggestions?" Shisui added, one eyebrow cocked. 

Itachi slumped down in his seat. "I… wanted to know if you two would be willing to help?" 

Obito shared another look with Shisui. It was  _ certainly  _ a surprise. Of course, Obito didn't necessarily have a  _ problem  _ with the suggestion.  _ Kami knew _ he had slept with Shisui enough to negate any argument towards that. 

"You uh… you're sure? Why  _ us? _ " Shisui asked quietly. 

Shisui seemed strangely subdued, and Obito had to wonder if he was  _ truly  _ okay with sleeping together with his younger cousin. They had practically grown up together, right up until Itachi's father had kicked him out and Shisui joined the crew. 

"I… I don't  _ want  _ to have to sleep with someone else. But… I won't try to force Kisame into that situation. I  _ trust  _ you. Both of you. And I am more than aware that you have no reservations about being with family." Itachi admitted softly. 

"I think Shisui and I should probably discuss this for a minute." Obito replied softly, placing one hand on Itachi's thigh reassuringly. He squeezed with his hand, and stood up to lead an awfully quiet Shisui into the hall. 

Even once the door was shut, Shisui didn't say anything. Obito put one finger under his chin, prompting his beautiful cousin to look at him. 

Shisui  _ was  _ stunning. He had been for as long as Obito knew him. Itachi was pretty in a feminine way, his slim bone structure and long hair making him look like something from a tv show. Shisui was more of the conventional style of handsome, with a wonderful jaw line, hair that perfectly framed his face, and beautiful large eyes. Supposedly,  _ all  _ members of the Uchiha were stupidly gorgeous. 

Obito wasn't entirely sure how  _ he  _ fit into that equation. Of course, he had been  _ told  _ he was beautiful plenty of times. His crew was not skimpy in their endorsements during sex. 

No matter how pretty Shisui was, Obito wouldn't agree to this unless the younger man was sure. Obito was older than both of them, and felt responsible for the situation at hand. "Shisui, do you  _ want  _ to do this?" 

Shisui blushed, and Obito was starting to wonder if maybe he wasn't  _ uncomfortable  _ at  _ all _ . Maybe the teen was just so  _ shocked  _ at the offer that he couldn't even comprehend it. 

Shisui and Itachi were close. Close enough that Shisui was  _ always  _ talking about Itachi.  _ Maybe  _ there was more to it than that. Maybe Shisui's love of Itachi was  _ more  _ than that of a familial variety, and he had never thought he'd get this chance. 

Obito waited as Shisui worked through his thoughts. The younger man bit his lip, meeting Obito's gaze with those expressive eyes. "I do. It's just…  _ unexpected. _ " 

Obito smiled, gripping Shisui's shoulder and pulling him in for a hug. Shisui all but collapsed into the older man's arms, and Obito fought back a laugh. 

"Okay. As long as you're sure." He commented, giving Shisui one more chance to object. 

Back in the room, Itachi was waiting calmly for them. He watched as the older Uchihas filed back into the room, one sitting on each side of him again. "Will you help me?" He asked quietly. 

"Are you sure you want  _ both  _ of us to help you?" Obito asked. It was one thing to want help… another thing to jump  _ right  _ into a threesome. 

Itachi nodded, looking up to give Obito a rare smile. "I don't think I will give myself another chance to do something like this once I am with Kisame. I really care about both of you, and I wanted to share this with you."

Obito couldn't help the giant grin that spread across his face. He was happy to share such an important moment with the teen. 

Shisui was too, apparently, because he took the initiative to tackle Itachi backwards onto the bed. 

They were kissing, and Obito's brain stopped working.  _ Shisui was kissing Itachi _ . The older of the two was straddling Itachi's lap, passionately kissing him down into the mattress. 

Obito huffed a laugh, crawling up the bed to get a better view. After a minute, Shisui sat up, hands placed gently on Itachi's chest. "So… I'm assuming you want to  _ bottom _ . But did you have any  _ other  _ thoughts on what you wanted to do? There  _ are  _ two of us." Shisui announced, his usual bubbly personality back in full force. 

Obito unhooked his scabbard and dropped his sword onto the floor. He wasn't even sure why he had  _ brought it _ . 90% of the time they were using  _ chakra _ . It wasn't often that he actually used the damn thing. 

"I… hadn't honestly thought about it. I just saw the two of you walking together, and knew that I wanted to ask." Itachi admitted, his face lighting up in a bright blush. 

Shisui giggled, shifting his hips with purpose over Itachi's waist. "Well… did you want to  _ top  _ at all?" 

Itachi was usually a very stoic person. He was level-headed, and calm even when everything was falling apart. That was what made it so shocking when he had very clearly already lost his composure. Shisui continued rubbing down onto him, the invitation perfectly clear. 

"I uh… I think I might… enjoy that as well. But I am more concerned with bottoming." Itachi ground out, dropping his head back onto the mattress with his mouth propped open. 

Obito huffed his amusement, leaning over to unbutton Shisui's shirt and toss it to the floor. He tried to contain his surprise at the purplish marks that littered his skin. Shisui was a  _ very  _ sexual being, and one of his definite kinks was that he enjoyed  _ being bitten _ . 

Naturally, that meant that the younger man was constantly falling into bed with Kakashi, who was the mouthiest lover on the crew. 

He shouldn't have been surprised. He had  _ known  _ that Shisui was almost always covered in marks of some sort. In fact, Obito could tell which marks were from  _ Kakashi _ … and which ones were from everyone else on the crew. The ones up by his neck were from Tenzo, and the darker ones around his waist were from Gai. Around his wrists, he had lines from where Minato had used his cuffs, and where Shisui had likely refused to let him heal the wounds. 

Itachi was also staring at his cousin, tracing some of his love-bites with his thumb. He didn't seem to  _ mind  _ the marks, likely more curious than anything. Obito thought it was  _ incredibly  _ sexy, and could feel his mouth watering at the sight. 

Shisui went to work, ignoring his cousins and their staring, and started pulling off Itachi's clothing. The younger teen was pliant, moving wherever Shisui guided him to. 

"Itachi… Kisame is  _ that  _ big? Have you seen it?" Obito asked curiously. It's not that he was  _ interested _ … but maybe they needed to do a little bit more to help Itachi work up to it. 

"I have, yes. It is  _ quite  _ impressive. I wasn't aware that they  _ could  _ be so large." Itachi answered, his entire chest flushing red at the thought. 

Obito shared one glance with Shisui, and decided that they would do all they could to help Itachi out. "Alright. We can help you." He replied. 

Itachi seemed elated that they were willing, even though that should have been more than obvious, considering they were all half naked now. 

Obito shed his clothing on his own, his large black eyes turning crimson to watch the scene unfolding before him. 

Shisui and Itachi were kissing again, but the older of the two had shifted his weight out of Itachi's lap so they could work their pants off. 

They were both so incredibly  _ attractive _ that Obito was starting to feel a bit out of place. Perhaps he didn't belong here. Not with  _ them.  _ Not when they both were so perfect that they appeared to be chiseled from  _ marble.  _

Shisui saw right through him, as he always did, pausing his attentions on Itachi to turn to him. "Obito." He called quietly, and Obito had no choice but to go. Shisui was a siren, pulling him in with his velvety smooth voice. 

"Stop looking so distraught, cousin." Shisui said with a smile, pulling Obito in for a wonderful kiss. Their lips danced together with practiced ease, even as Shisui seemingly stole all of the air from Obito's lungs. 

Once they broke away for air, he saw the sharingan in two sets of eyes  _ other  _ than his own. Something inside Obito's head could hear Tenzo lecturing them about the misuse of chakra… but he ignored it. It was too  _ hot _ . Everyone here would have a crystal clear memory of what happened.  _ None of this  _ would be forgotten. 

Obito moved to Shisui's side, leaning down and taking  _ his  _ first kiss from Itachi. Despite his inexperience, he learned quickly, emulating Shisui's kissing earlier. 

Itachi suddenly moaned into his mouth, and Obito could only  _ imagine  _ what Shisui had gotten started on. Another moan, and Obito pulled away, only to see Itachi's cock enveloped by Shisui's sinful lips. 

Shisui was skillful in  _ all  _ things, and Obito had to wipe a bit of drool as he watched his cousin take Itachi to the base easily. He understood, of course. It would be easier to penetrate Itachi if he was relaxed. Obito returned to capture Itachi's mouth, the kiss hurried and messy when Itachi couldn't seem to keep his voice down. Honestly, Obito hadn't expected Itachi to be so  _ vocal.  _ The younger boy was flushed, his pale skin glistening with sweat and his arms shaking the smallest amount. Obito couldn't keep his eyes off of him, because he knew he would be  _ wrecked  _ by the time they were done with him. 

Obito descended upon his chest, mouthing along soft skin and nearly growling when shaky fingers found their way into his hair. When Obito's warm lips closed around Itachi's cute little nipple, his back arched off the bed, the loudest moan yet escaping from his lips. 

It wasn't long after that when Shisui's slurping noises slowed, and Itachi's body tensed up. His arms dropped to the mattress, and his labored breathing told Obito everything he needed to know. 

Of course, Shisui had a large grin on his face, overly proud of the way he had unraveled Itachi so far. 

_ They still had a long way to go _ . 

Nearly half an hour later and Obito found himself two fingers deep into Itachi's ass. He was  _ so tight _ , and he could only imagine what it would be like to finally fuck the younger boy. Itachi was squirming, restless as Shisui made for a wonderful distraction. Itachi was already turning purple in several places. Shisui was attacking his skin with vigor, as if he had been waiting for this moment for quite some time. 

Obito smirked at every moan and jump that he caused in the younger man. His fingers curled and worked Itachi's tight muscles, spreading and massaging until there was enough give to add a third. The body beneath him shook when Obito finally got around to adding a third finger, Itachi's moans filling the room. 

Obito held back a groan. listening to his cousin moan so openly when the younger boy had been nothing but quiet for the longest time was almost too much. Shisui was having a hard time as well, growling softly as he pressed kisses into the pale skin beneath them. 

Finally, he deemed the younger man fully prepared. 

But who would go first? 

Obito glanced over to Shisui, the excitable man nearly vibrating out of his skin in anticipation. The older man sighed half-heartedly, pulling his fingers out slowly and beckoning Shisui over.

They didn't train under Minato for nothing, the younger man flickering over before Obito could blink. 

Once Obito was out of the way, Shisui wasted no time slicking himself up and pressing his cock against Itachi's tight entrance. Obito was up by the younger man's ears, whispering sweet encouragements to his heavily breathing cousin and running his hands up and down his sides. 

If he didn't know any better, Obito wouldn't think that Itachi was a virgin. He calmed himself plenty without Obito's help, but that didn't deter him one bit.

Shisui pushed inside with little resistance, Itachi moaning beneath him. Obito bit back a groan of his own, watching Itachi's face contort with the stretch. It was very clear when the strange feeling of being penetrated gave way to pleasure. Itachi's body relaxed, and his breath hitched as Shisui waited for him to adjust.

Shisui looked like he was having an excessively hard time keeping still. His fingers shook and gripped Itachi's hips tightly, and his mouth was held open. Obito took the opening for what it was, leaning back to capture Shisui in a kiss as well. Itachi was watching. Why wouldn't he? He had clearly expressed an interest in both of them, and what harm would there be in putting on a little show?

Shisui groaned into the kiss, his hips jutting forward the smallest amount and knocking all of the breath from Itachi's lungs. Obito couldn't help but grin, enjoying the chain reaction but making sure not to do it again. 

Shisui finally started to move. Slowly at first, though Obito would be the first to admit that he wasn't very good at taking things slow either. He leaned down to distract Itachi some, leaving more purple marks down his cousin's chest until he reached his prize. Gripping Itachi's hardening cock in one hand, Obito licked his lips. Itachi and Shisui were both watching him, even as Shisui rocked into Itachi's tight ass. 

Neither of them were quiet, and Obito was lost to the beautiful sounds dripping from both of them. Surely, if he died right at this moment, he would only return here because  _ this _ was heaven. Obito was sure of it. 

Itachi was mumbling, his normally soft voice spilling out between cries as Shisui focused all of his attention on hitting that tiny bundle of nerves within the younger man. 

Obito paused the movements of his hand, giving Itachi's cock a small squeeze before dipping down and swallowing him whole. 

Itachi cried out sharply, his back bowing off of the bed with the pleasure of the dual sensations. Obito barely managed to back up as Itachi thrust forward sharply, narrowly avoiding being choked on the cock that was twitching in his mouth. 

Suddenly, Obito was grateful for the silencing seal he had slapped on the bedroom wall when he had originally rented the room, because Itachi's cries would undoubtedly get them kicked out otherwise. 

Obito could tell by the sound of Shisui's groaning that the younger man was close, and he made a serious effort to bring Itachi close to the edge as well. His tongue swirled around the cock in his mouth as he hollowed his cheeks and sucked harshly. 

Obito was rewarded when Itachi nearly  _ wailed _ while orgasming into Obito's mouth. 

Swallowing Itachi's release was easy. The  _ tricky part _ was trying to dodge Shisui's when he pulled out of Itachi's ass and shot his seed onto his stomach instead. Obito  _ just barely  _ missed having a face covered in come, though it was hard to be grumpy when Shisui looked so utterly blissed out. 

Once he recovered, Shisui moved to the side, leaning down to kiss Itachi slowly. Obito quickly took his place, gingerly working a finger back inside of his younger cousin. Itachi’s breath hitched, but Obito didn’t take things any further. Not yet. He would give Itachi a few minutes to wind down from his second orgasm of the night. 

Watching the two of them kiss was not something Obito would be forgetting anytime soon, especially not with the sharingan swirling lazily in his head. The sweet emotions passing between their lips were soft, and distracting in the way that Obito simply couldn’t pull his eyes away from them. 

Eventually, Itachi started squirming, rocking his hips and shifting his legs in an attempt to gain some friction on the lone finger inside of him. Obito took the hint, adding another finger and checking to make sure Itachi was still stretched properly. 

They still had more work to do, after all, if Itachi was to be prepared to take someone of Kisame’s apparently massive size. 

Obito didn’t waste much time, carefully removing his fingers and lining up with his slicked up cock inside. There was little resistance when he slid inside of Itachi’s pliant body, his muscles still relaxed from taking Shisui earlier. Itachi mewled, happy to once again be filled, and moving easily when Obito grabbed his legs and lifted them. He didn’t stop until Itachi was nearly bent in half, holding off on his thrusts until Shisui happily took over holding the younger man’s legs. 

Shisui kept Itachi’s mouth busy, kissing him languidly while Obito started to move, slowly pulling back. He watched closely as Itachi’s ass stretched around his cock, swallowing him hungrily as he pressed back in. 

On the next thrust, Obito carefully held a finger alongside his cock, watching as the pink skin stretched that much further to accommodate the extra girth. Itachi mewled, clearly enjoying the extra finger being added. Obito smirked, locking eyes with Shisui for only a moment as he watched curiously. Shisui’s eyes widened as Obito thrust in shallowly, keeping his finger straight even as he slowly added a second. 

Itachi whined wantonly, his voice higher pitched than either of them had ever heard it. Obito fought off a devious grin as he listened, though the realization that Itachi was absolutely  _ loving this _ made it difficult. 

Itachi’s fingers clawed at the sheets when he added the third finger, lining his cock with the digits and carefully surging forward. The younger man was nearly thrashing, his face sweaty and red with ravenous lust. Shisui was murmuring more encouragement into Itachi’s ears, brushing his sweaty hair out of his face and caressing his skin gently. 

It was  _ beautiful.  _ Obito could hardly hold himself back as he continued his slow ministrations. Shisui was fisting his own cock, dutifully keeping Itachi’s legs up and nosing along the younger man’s jaws while Obito kept stretching him further. 

Obito had only done this twice before. Once, Gai and Obito had worked together to take Kakashi at the same time, stretching the wolfy man until his fanged jaws were snapping wildly in the open air, his instincts taking over in the throes of passion. The other time, Tenzo and Kakashi had both stretched Obito far past his limits and had ridden him until he couldn’t walk straight for  _ three days. _

Both times had been wonderful.  _ Beautiful  _ even. But neither of them could compare to the look on Itachi’s face when Obito added a fourth finger, and he realized where this was headed. Itachi came for the third time with Obito’s cock and four of his fingers buried deep in his ass. The muscles had clenched so tightly that Obito was afraid his fingers would be crushed, but he held steady anyway. After Itachi had come down from his high, Obito was able to flex his fingers, gently probing as deep as he could. 

Itachi was as ready as he would ever be, and Shisui knew it too. Itachi’s legs dropped to his side when Shisui released them, and the youngest hardly reacted when Obito wrapped his arms around him and flipped them over. Obito laid on his back, Itachi nothing more than a limp weight on his chest. He smoothed long black strands out of Itachi’s face, trying to get the hazy crimson eyes to meet his own. 

“Itachi.” He cooed softly, unwilling to move forward until the nearly delirious man gave his permission again. The younger man finally tilted his head, meeting Obito’s gaze. “Do you want to continue?” Obito asked. Itachi was smart enough to understand exactly what he was referring to, even without glancing back towards Shisui, who had taken up his new spot behind him. Shisui was sliding his fingers into Itachi’s ass slowly, replacing the ones Obito had removed to flip them. Shisui was groaning softly, and Obito was struggling to remain still as foreign fingers slid along his cock. 

“Yes.” Itachi replied breathily, shivering as Shisui added a fourth finger. “I want to continue.”

Shisui nearly whined in response, his eyelids fluttering shut as he continued to finger Itachi’s ass. “Alright.” 

Obito could feel Shisui’s fingers retreating, and braced himself for the inevitable arrival of Shisui’s cock. Itachi whimpered when the last finger left, rocking his hips slowly as he waited. Obito wasn’t sure if  _ any  _ of them were breathing when Shisui’s cock nudged at the tight ring of Itachi’s ass, and Obito forced himself to concentrate. He pressed his lips against Itachi’s, trying to ground the shaking body above him. 

Shisui exhaled loudly, his cock sliding against Obito’s as he worked his way in. Itachi broke away from the kiss, moaning loudly and digging his fingers into Obito’s chest. Obito growled, nipping at Itachi’s neck and collarbone. The world froze for a moment when Shisui was finally all the way in, the three of them simply attempting to breathe. 

“Itachi?” Shisui gasped. “Are you alright?”

The words that Itachi tried to say came out as a whimper, but he nodded softly as well. 

“You’re doing great, Itachi.” Obito cooed, running his fingers through long strands of hair. 

Eventually, Shisui moved experimentally. Obito’s voice cracked as he cried out, his grip on Itachi’s waist tightening accidentally. He was more prepared for the next movement, carefully sliding out as Shisui slid in, building up a slow rhythm while Itachi continued to cry himself hoarse. Obito had never experienced a partner so…  _ enthusiastic. _ Itachi was very clearly enjoying every second of this, and Obito couldn’t help but think that he was likely the  _ perfect match _ for someone like Kisame. 

Shisui started moving faster, and Obito could hardly think of anything other than the tight flesh gripping them both and the wanton cries filling the air. It was unclear which moans came from who, since all three of them were unable to contain themselves at all. Obito knew the moment that Itachi came for the fourth time that he couldn’t hold back any longer. The tight grip on his cock unraveled him, the oldest of the three nearly shouting his release as white flooded his vision. Obito was lost to his pleasure, and he wasn’t really sure how long he had been out of it. What he  _ did  _ know was that he was now supporting the weight of  _ both  _ of his cousins. Shisui had collapsed on Itachi’s back, and Obito’s softened cock was no longer nestled in Itachi’s ass. None of them spoke. None of them  _ could  _ speak. The three Uchihas simply tried to catch their breath once again. 

After a few minutes, it had become clear that Itachi was asleep. Shisui groaned softly as he pried himself from Itachi’s sweaty back, his arms shaking as he attempted to help Obito dislodge himself from under the youngest. They worked together to lower Itachi onto the mattress, the man completely unconscious from his exhaustion. Even asleep, Itachi looked beyond happy. Both of them watched him for a few moments in silence.

“I think it’s safe to say he enjoyed it.” Shisui whispered softly, his voice raspy. 

Obito huffed a laugh, reaching down to move a few loose strands of hair from his face. “Yeah. I’d say so. Do you think that was enough?”

Shisui chuckled that time, though it wasn’t loud enough to wake Itachi. “If  _ that  _ wasn’t enough, I think Kisame needs to get that thing looked at.” 

Obito huffed. That… wasn’t entirely what he had meant. Even though Itachi had taken both of them with enthusiasm, he couldn’t help but worry. He didn’t really  _ know _ Kisame. The older man had always kept to himself. Truthfully, it was a bit surprising that he and Itachi had gotten along so well. 

“Obito…” Shisui started, “I know you’re worried. But Itachi is smart. He wouldn’t even want to get  _ involved _ with Kisame if the guy wasn’t something special.”

Obito turned to meet Shisui’s gaze. He seemed more than confident in his assessment, and Obito was inclined to believe him. Shisui had known Itachi for far longer than Obito had, after all. “Okay.”

Shisui smiled, threading his fingers through Obito’s. “Of course, that doesn’t mean we shouldn’t give the guy some sort of  _ initiation _ . After all, Itachi  _ is _ family to us. He should have our approval.” 

Obito laughed, half wondering what sort of crazy ideas were floating through his cousin’s head… and half concerned. “Let’s not give him  _ too _ hard of a time. After all, he clearly put Itachi’s well-being above any urges he had. He gave away Itachi’s  _ virginity _ just to ensure that he wouldn’t hurt him.” 

Shisui hummed, returning his gaze to the sleeping man. “That’s fair, I guess. Maybe we should get him cleaned up now.”

Obito and Shisui worked together to clean the excessive amount of mess they had made. Itachi didn’t stir once during the process, and Obito couldn’t help but be proud of how thoroughly they had worn him out. Obito moved the rest of the mess, while Shisui sent some healing chakra through Itachi’s system. He wouldn’t be hurting  _ too _ badly in the morning… but he would certainly be feeling what they had done for at least a full day. 

Once they settled down for the night, Obito and Shisui both cuddled around their younger cousin, sharing their warmth and letting exhaustion pull them to sleep as well. 

~

Walking around the village the next morning was a slow process. Obito and Shisui were tired, and they could only imagine how tired and sore Itachi must have been. Still, he carried himself wonderfully, and even picked up his pace when they spotted Kisame and Sasori. 

Shisui and Obito hung back while Itachi spoke with the man he was clearly very attached to. They didn’t feel awkward until Itachi smiled, pointing at them both. Obito hadn’t been aware that Kisame could blush, but the blue colored skin was definitely tinting red as his mouth widened in surprise. 

It was almost enough to make Obito laugh to see someone as tiny as Itachi drag someone of Kisame’s size around by his hand. At least it  _ would _ have been, if he hadn’t been dragging the giant straight towards them. Thankfully, Sasori chose to stay back, propping himself up against a building and examining his fingernails.

Shisui chuckled as they walked up, smiling brightly at Itachi’s obvious fondness. “Careful, Kisame. Once you let him start bossing you around, it never ends.” 

Itachi playfully glared at Shisui, though the joke was enough to erase the awkwardness of the situation. The large man cleared his throat, wrapping an arm around Itachi’s shoulders. “I think it’s a bit too late for that.” 

After a few more minutes of conversation, and a very wholehearted  _ thanks  _ from Itachi, Shisui and Obito ran off to meet up with their crew. 

Normally, sailing away from their sister ship was a bittersweet affair. It was nice to be back on the open seas again, but there was also the disappointment of watching their cousin disappear along the horizon. 

This time, however, Obito couldn’t help but smile as Kisame and Itachi stood side-by-side on the deck of  _ The Akatsuki _ and waved goodbye. Itachi was happier than he had ever seen him, and even Shisui seemed to agree with that sentiment. Warmth filled his chest as their ships continued sailing away from each other. 

Of course, it was always quiet moments like this that Shisui chose to say something absurd. “We’ll have to ask him about sex with Kisame when we see him again.” 

Obito huffed and rolled his eyes, trying not to smile at his perverted cousin’s suggestion. Of course, Obito knew it would be a race to see who could ask him first. 

**Author's Note:**

> Thank you @anannua for such an amusing prompt that I was able to add to my pirate series! I hope you enjoyed it.  
> P.s. this is my first attempt at writing double penetration... and I don't think it will be my last! 😉
> 
> Let me know what you think! Comments always make my day!


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